ID: ALA3319483

Max Phase: Preclinical

Molecular Formula: C37H44N4O5

Molecular Weight: 624.78

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1=C(C(=O)N[C@H](C)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@@H](CC2CCCCC2)C(=O)[C@@]2(C)CO2)Cc2ccccc21

Standard InChI:  InChI=1S/C37H44N4O5/c1-22-27-14-8-7-13-25(27)18-29(22)35(44)39-23(2)34(43)41-32(19-26-20-38-30-16-10-9-15-28(26)30)36(45)40-31(33(42)37(3)21-46-37)17-24-11-5-4-6-12-24/h7-10,13-16,20,23-24,31-32,38H,4-6,11-12,17-19,21H2,1-3H3,(H,39,44)(H,40,45)(H,41,43)/t23-,31+,32+,37-/m1/s1

Standard InChI Key:  HCSMZVMWZMSHSC-LZNHGOJSSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 624.78

Molecular Weight (Monoisotopic): 624.3312

AlogP: 4.54

#Rotatable Bonds: 12

Polar Surface Area: 132.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.24

CX Basic pKa:

CX LogP: 5.33

CX LogD: 5.33

Aromatic Rings: 3

Heavy Atoms: 46

QED Weighted: 0.22

Np Likeness Score: 0.26

References

1. de Bruin G, Huber EM, Xin BT, van Rooden EJ, Al-Ayed K, Kim KB, Kisselev AF, Driessen C, van der Stelt M, van der Marel GA, Groll M, Overkleeft HS..  (2014)  Structure-based design of β1i or β5i specific inhibitors of human immunoproteasomes.,  57  (14): [PMID:25006746] [10.1021/jm500716s]

2. Xin BT, de Bruin G, Huber EM, Besse A, Florea BI, Filippov DV, van der Marel GA, Kisselev AF, van der Stelt M, Driessen C, Groll M, Overkleeft HS..  (2016)  Structure-Based Design of β5c Selective Inhibitors of Human Constitutive Proteasomes.,  59  (15): [PMID:27438186] [10.1021/acs.jmedchem.6b00705]

Source

Source(1):

• Scientific Literature